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5-Benzyl-5-azaspiro[2.4]heptane-4,7-dione → 5-Benzyl-5-azaspiro[2.4]heptan-7-ol

HRID 1366495
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1366495
[C:1]1([CH2:7][N:8]2[CH2:14][C:13](=[O:15])[C:10]3([CH2:12][CH2:11]3)[C:9]2=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[C:1]1([CH2:7][N:8]2[CH2:14][CH:13]([OH:15])[C:10]3([CH2:11][CH2:12]3)[CH2:9]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 98777875-Benzyl-5-azaspiro[2.4]heptane-4,7-dioneHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 584529235-Benzyl-5-azaspiro[2.4]heptan-7-olAusbeute 104,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

5-(Phenylmethyl)-5-azaspiro[2.4]heptane-4,7-dione (997.4 mg, 4.63 mmol) was dissolved in 46 mL of THF and LiAlH4 (997 mg) was added portion wise with stirring. The mixture was heated to 65° C. for 5 hours, then cooled to 0° C. The reaction was quenched with Na2SO4.H2O and was stirred at room temperature overnight. The contents were filtered through Celite, and the Celite pad was washed with EtOAc. The Celite filter cake was suspended in EtOAc (200 mL) and boiled for 5 min. The suspension was filtered, and the combined organic filtrates were then concentrated in vacuo to provide 5-(phenylmethyl)-5-azaspiro[2.4]heptan-7-ol (983 mg, >100%). LCMS: (M+H)+: 204.1

Aufarbeitung

  1. temperaturecooled to 0° C
  2. customThe reaction was quenched with Na2SO4.H2O
  3. stirringwas stirred at room temperature overnight
  4. filtrationThe contents were filtered through Celite
  5. washthe Celite pad was washed with EtOAc
  6. filtrationThe Celite filter cake
  7. filtrationThe suspension was filtered
  8. concentrationthe combined organic filtrates were then concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-ab64afb184ff459ab687d209604f942d
Quelldatensatz
uspto-grants-2011_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07893056B2

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